1609137-34-9Relevant academic research and scientific papers
Orthogonal Recognition Processes Drive the Assembly and Replication of a [2]Rotaxane
Kosikova, Tamara,Hassan, Nurul Izzaty,Cordes, David B.,Slawin, Alexandra M. Z.,Philp, Douglas
, p. 16074 - 16083 (2015)
Within a small, interconnected reaction network, orthogonal recognition processes drive the assembly and replication of a [2]rotaxane. Rotaxane formation is governed by a central, hydrogen-bonding-mediated binding equilibrium between a macrocycle and a linear component, which associate to give a reactive pseudorotaxane. Both the pseudorotaxane and the linear component undergo irreversible, recognition-mediated 1,3-dipolar cycloaddition reactions with a stoppering maleimide group, forming rotaxane and thread, respectively. As a result of these orthogonal recognition-mediated processes, the rotaxane and thread can act as auto-catalytic templates for their own formation and also operate as cross-catalytic templates for each other. However, the interplay between the recognition and reaction processes in this reaction network results in the formation of undesirable pseudorotaxane complexes, causing thread formation to exceed rotaxane formation in the current experimental system. Nevertheless, in the absence of competitive macrocycle-binding sites, realization of a replicating network favoring formation of rotaxane is possible.
Rotaxanes synthesized through sodium-ion-templated clipping of macrocycles around nonconjugated amide and urea functionalities
Ho, Tsung-Hsien,Lai, Chien-Chen,Liu, Yi-Hung,Peng, Shie-Ming,Chiu, Sheng-Hsien
, p. 4563 - 4567 (2014/05/06)
A single urea or amide functionality in a dumbbell-shaped guest can be clipped by a macrocycle generated from a diamine and a dialdehyde through the templating effect of a Na+ ion (see scheme). The resulting imine-containing rotaxanes can then be reduced to allow isolation of stable amine-based rotaxanes. A single urea or amide functionality in a dumbbell-shaped guest can be clipped by a macrocycle generated from a diamine and a dialdehyde through the templating effect of a Na+ ion (see scheme). The resulting imine-containing rotaxanes can then be reduced to allow isolation of stable amine-based rotaxanes.
